Summer Festivals on the Chesapeake Bay


Summers on Maryland’s Eastern Shore offer plenty of fun for everyone. Kent County, in particular, has planned a variety of events this summer that will delight the young and old. Here’s a list of what’s coming up soon:

Music in the Park
June 23, July 7 & 21, and August 4 & 18
Grab your beach or lawn chairs and head to Fountain Park, in downtown Chestertown, to enjoy the best in local and regional music! Every other Saturday from 7-8:30 p.m., “Music in the Park” will feature a free concert highlighting all types of music including big band, bluegrass, folk, jazz, rock, and more!

July Fourth Week
July 1-7
Kent County always has fun parades and incredible fireworks displays on July 4th.

Kent County Fair
July 19-21
A traditional county fair, the Kent County Fair features a variety of traditional fair amusements such as: 4-H, community, agricultural, and animal exhibits, games, great food, entertainment and more!  Visitors can also watch a greased pig contest, bull-riding, and livestock auctions.

For more information about this event, and to check out the event schedule, visit the Kent County Fair website.

Betterton Appreciation Weekend
August 3-4
Appreciation Weekend kicks off with fireworks on Friday! On Saturday, follow the parade down Main Street to the beach, where all kinds of fun can be had! Listen to live music as you peruse the game, craft, and food stands that line the beach. Please call 410-348-5678, or visit the Betterton Volunteer Fire Company website for more information.

Pirates and Wenches
August 10-12
Calling all buccaneers and land lubbers – come by land or by sea to Rock Hall’s annual Pirates and Wenches Festival. Prepare your dinghy for the Decorated Dinghy Contest, followed by a Poker Run. Sing sea shanties and drink your fill of rum at Osprey Point’s rum tasting. From kiddie costume contests to a pirate ball, there is fun to be had by all! This is one festival, you won’t want to miss!

Chestertown Jazz Festival
September 6-10
The Chestertown Jazz Festival is an electrifying collaboration between Rock Hall’s Mainstay Theater and Chestertown’s Garfield Center for the Arts, as well as local influencers. This four-day jazz and blues extravaganza will feature full days of sensational jazz entertainment and local food, wine, and beer. Enjoy the swingin’ sounds of jazz, while the beauty of Maryland’s Chesapeake Bay surrounds you.

You’ll love spending some time on the beautiful Chesapeake Bay. Call Great Oak Manor at 410-778-5943 to reserve your stay!